Acetic Acid → HCID 43608425, compound

HRID 341173Notes

Reaction equation

HRID 341173 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[CH:6][CH:7]=1.[O:9]1[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][CH:12]2[CH2:13][CH2:14][O:9][CH2:10][CH2:11]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 115623-BromoanilineHCID 121599Tetrahydro-4H-pyran-4-oneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 43608425HCID 43608425, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 3-Bromo-phenylamine (0.54 ml, 5 mmol) and tetrahydro-4H-pyran-4-one (0.5 g, 5 mmol) in DCE (20 ml) was added sodium triacetoxyborohydride (1.48 g, 7 mmol) and acetic acid (0.3 g). The mixture was stirred for 18 h before being quenched with 1N NaOH (10 ml). The mixture was partitioned between Et2O and H2O, the aqueous layer further extracted with Et2O, the organics combined, dried (MgSO4), filtered and the solvent removed in vacuo to give a colourless liquid. Purification using silica column chromatography (0-80% EtOAc/hexane gradient) afforded the title compound as a white solid (0.81 g). MS: [M+H]+=256,258

Workup

  1. custombefore being quenched with 1N NaOH (10 ml)
  2. customThe mixture was partitioned between Et2O and H2O
  3. extractionthe aqueous layer further extracted with Et2O
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customto give a colourless liquid
  8. customPurification

Sources & evidence

ORD record
ord-74f7e099c31c431c99a86aa17032ddd6
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

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